Trans/Sex: Masturbation is tough for trans women. I know first-hand

Trans/Sex is a column about trans peoples’ relationships with love, sex, and their bodies. Have a topic suggestion? Contact Ana Valens at [email protected] or @SpaceDoctorPhD on Twitter.

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The other night, it took me a full hour to orgasm: first by stroking myself up-and-down with lube, then switching to my Hitachi Magic Wand. I wanted to cum as much as I possibly could to see if I could earn multiple orgasms in one session. It didn’t work out. Sore, spent, and ridiculously turned on, I put away my Hitachi, took a 2am bathroom break, and went to sleep.

This is a common problem for me. Despite the fact that I love talking on and on about sex and fetishism and girldick, the actual physical act of touching myself became a challenge after I started taking estrogen. Don’t get me wrong, I’ve had my fair share of phenomenal cums and exhilarating, full-body orgasms since beginning hormone replacement therapy (HRT). And I’ve had plenty of good sex over the years. But increasingly, I find myself feeling frustrated and stressed out when I go to masturbate. It’s like I can’t figure out how this thing works. I suspect other trans women feel the same way.

So when I sat down to write this column, I decided to create a challenge for myself: By the end, I wanted to figure out how to masturbate. Come along with me, it’s going to be a bumpy ride.

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Before I get into the nitty-gritty behind my own “alone time” sessions, it’s worth rehashing why masturbation is so complicated for trans women. For many of us, we undergo HRT regimens that change the way our penises physically function. As estradiol continues to feminize our genitalia, the skin on our clit becomes softer, thinner, and more fragile. We stop having random erections in public, and the penis may atrophy. This means the actual act of getting fully hard becomes much more difficult, if not outright impossible, without access to erectile dysfunction medications like Viagra.

All this isn’t necessarily a problem, as there are plenty of ways trans women can touch themselves (and orgasm!) without an erection. But for most trans women that went through puberty on testosterone, our assumption is that a penis must be as hard as possible to cum. Breaking down that belief during those first few months on HRT can be a difficult and challenging adjustment period.

I knew that my penis would change on HRT, but I didn’t realize just how different masturbation would be. That’s because there’s barely any sexual literature out there for trans women looking to pleasure themselves. Fucking Trans Women by Mira Bellwether and Girl Sex 101 by Allison Moon are the few exceptions that come to mind, featuring comprehensive overviews on how to handle and touch girldick. But there’s no comprehensive masturbation book for pre-op and non-op trans women who want, say, dozens of masturbation techniques to try out. The best resource we have is Bellwether’s zine, which features an in-depth explanation of how the genital region operates in trans women and the corresponding areas one should touch based on their physical build. Otherwise, you have to ask other trans women for advice, scourge through subreddits like r/asktransgender for ideas, or have sex with other trans women who can pass on some of their knowledge.

All this is to say that masturbation isn’t as simple as sitting down and stroking up and down until something comes out. One trans woman I spoke to, Cassidy Frank (who uses they/them pronouns), compared masturbating on HRT to driving a car on manual, complete with shifting gears “at the right speeds/moments” to maintain momentum and “not get numb to the sensation.” It’s an apt metaphor: Most drivers can barely handle a car on automatic, let alone driving stick. And while Frank knows their way around their genitalia, it’s not as if those skills easily transfer to their sexual partners.

“In my four-and-a-half years of HRT, not once have I achieved orgasm during sex with another person except when I just stop the action and get myself off,” Frank told me over email. “Sex partners tend to feel inadequate and I end up comforting them at the end of sex. […] I don’t know how to teach someone else how to make my genitals work, I feel like I need someone to teach me.”

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When I use the Hitachi Magic Wand Wireless, I’ll either strip down naked (with or without panties), throw a sheet over me, and press the wand right on or near my frenulum (the intersection between the shaft and the head). I’ll shift my placement and pressure depending on how my body responds, and I’ll try to zone out and just follow wherever my mind wants to take me. It’s given me some incredibly hot full-body orgasms over the years, the kind where I can barely control myself and start squirming and whimpering when I’m done. (I’ll also use the Le Wand to similar effect.)

But there’s a downside to masturbating this way: If I use these vibrators for too long, they can cause my clit to feel numb and sore from too much sensation. In worst case scenarios, it can cause tearing or rawness. That means when I’m particularly stressed out, or if I’m nervous about cumming before the soreness begins, it can ruin my headspace and cause me to feel disconnected with my body while masturbating.

There are other, less complicated ways I touch myself. Sometimes when I’m turned on but completely soft, I’ll start stroking myself, watching or listening to porn, and fantasizing until my clit starts to become slightly erect. Then I’ll pull out a bottle of Babelube and stroke myself. Usually, I’ll do this by laying down and cupping the side of my cock with my palm from the left or right side while I stroke my fingers across the back of the shaft, running my thumb up and down the front. Occasionally, I’ll flick the tip, but it’s very, very sensitive, and easy to overdo. If my mind is in the right place and I’m starting to get closer and closer to an orgasm, I’ll usually reposition my hands into a fist and start jerking up and down until I finish. I’ve had some incredible orgasms this way, and many of these are easier to reach without any of the rawness or soreness I’ve experienced with my Hitachi. The downside to this, of course, is that it’s a little messier, it requires more clean up, it can be a little dysphoric, and it’s hard to look at porn if I’m doing this while laying down.

But that’s how I’ve masturbated for the past three years, at least for the time being. Frank seems to use a similar technique, although to greater effect. When I interviewed them, they explained that they “rarely have trouble orgasming,” and in some cases, they can even have orgasms three or four times in a row.

“What feels the best is to rub [my genitals] through my underwear,” Frank told me. “If I press down into my underwear and massage in circles, rubbing it, rubbing my hand and fingers up and down the shaft through the underwear, that feels the best. It does, uhhh, get messy on said underwear! But something about that specific friction through the clothing feels way better.”

To prevent themselves from staining their underwear, Frank will also take off their panties and “switch to an up-and-down motion” to reach a climax, not unlike myself. It doesn’t feel as good, but it helps with reaching an orgasm.

“I’ve found that if I can manage to, at juuuust the right moment, switch to massaging just the head with my fingers in a circular motion, and push myself over the edge while doing that, then the orgasm is much stronger and feels even better,” Frank explained, “but it’s difficult to get the timing right.”

There are other ways to masturbate too, of course. Colleen Potvin, a nonbinary trans woman who uses she/her and they/them pronouns, has been “off and on” HRT for the past five years. When I spoke to them over email, they told me that they prefer to masturbate by rubbing against their bed, “putting pressure on the whole of my genitalia.”

“I’ve always preferred it this way, and it’s pretty consistently the way I have to finish off a session,” Potvin told me. “I do occasionally use hands to start. I’ve tried a vibrator, but it feels awkward due to the dysphoria of using it on a penis when I really want it against a [vaginal] clitoris.”

There’s also “muffing,” a technique popularized by Bellwether in Fucking Trans Women. Simply put, muffing involves stimulating the inguinal canals, which are the internal pockets that house the testes when they recede within the body (and are also used to “tuck” our testes in for a flat front). For some trans women, playing with these canals is extremely pleasurable. In my case, it feels nice, but it doesn’t exactly turn me on. I’ll save my inguinal canals for tucking, not fucking, thanks.

Then there’s anal play through butt plugs and other toys, which can be used to stimulate one’s prostate to great pleasure. Other trans women like to play with their perineum, or the “taint” between the scrotum and the anus, by either placing a vibrator on it or stroking it. Many trans women call it their “cunt” or “pussy,” and with the right pressure, it feels phenomenal. That’s because the perineum is located parallel to the prostate.

For the record, stimulating the perineum, anus, and clit all at the same time can be incredible for trans women thanks to the nerve endings in each of these parts of the body, as Bellwether points out in Fucking Trans Women. When I was reading Bellwether’s zine for this column, that passage in particular stuck out to me. I had never tried focusing on both my clit and my perineum at the same time before. Remember how I mentioned above that it’s difficult to learn about one’s own body without meeting or having sex with other trans women? Case in point, I never knew how good the perineum could feel until I finally hooked up with a girl who fucked it in just the right place, and it blew my mind. As I would later find out while writing this column, touching my perineum the right way unlocked a new world of sexual pleasure that I never could have dreamed of before.

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This isn’t a comprehensive look at masturbation for trans women. The truth is, there’s no one-size-fits-all guide to touching ourselves and getting off. We’re all still learning how to handle our bodies and pleasure ourselves, in part because no one taught us how to touch our genitals and get to know them when we first started HRT. That means relearning how to masturbate may be a work-in-progress, one that’s best figured out through trial and error.

The more trans women I spoke to on- and off-the-record, the more I realized what I was doing wrong. I wasn’t experimenting with my body. I wasn’t listening to the sensations running through my arms and chest when I lightly graced them. I thought I knew how to touch myself, and I tried to do it by force. What I needed to do was relinquish control, play with my breasts and nipples gently, and listen to the signs my body was giving me while playing with myself.

After rereading Fucking Trans Women, I sat down and tried something I had never done before: really, specifically, fingering my perineum and touching myself. I had to take a minute to feel around and find the right spot, but once I did, it felt so, so good, like a rush of arousal flooding through my crotch and thighs. Finally, I cracked the code. I tried changing how I masturbated by using both my Hitachi and stimulating my perineum at the same time. It didn’t just work, it gave me one of the best orgasms I ever had, leaving me sprawling, spent, and incredibly satisfied.

I tried again later that week, fingering my perineum while using my Hitachi. And to my surprise, during my second round, my legs started shaking, my thighs quivering, my whole body struggling to stay together. I didn’t resist that wave; I rode it. And I came! Finally, a second orgasm! I withered and squirmed in a release I had never felt before. If this is what masturbation is supposed to feel like, then it’s really, really good. And if it wasn’t for rereading Fucking Trans Women and talking to trans women who figured out what worked for themselves, I might’ve never figured it out.

Looking back on my orgasms, I’m reminded of what Frank told me: Masturbating is like driving a car. They’re right, and I know I’m still learning how to drive. But I think I’m getting the hang of this thing, one ride at a time.

Ana Valens is a reporter specializing in online queer communities, marginalized identities, and adult content creation. She is Daily Dot's Trans/Sex columnist. Her work has appeared at Vice, Vox, Truthout, Bitch Media, Kill Screen, Rolling Stone, and the Toast. She lives in Brooklyn, New York, and spends her free time developing queer adult games.